That's a nice reconstruction. My old dead-tree Webster's Collegiate Dictionary has an essay in its foreword that covers the evolution of English in reverse order, ending with texts in Old Anglo-Saxon. The further back, the more alien it seemed. I'd need a lot of help with Middle English, and anything older would require the sort of major effort/rewriting discussed here. William the Conqueror set a huge linguistic change in motion with his little dust-up.

Really, even early Modern English (e.g. Shakespeare or the King James Bible) is pretty thick for today's English speakers.